Crossdressing in Public – Downtown Chicago

  • Crossdressing at The Baton LoungeYikes, I haven’t posted on my blog in a while, but don’t worry – I’ve still been crossdressing :) In fact, not long ago I was out for a night on the town in downtown Chicago all dolled up, so I thought I’d share a couple of the candid photos I took that night. Allie took me out to The Baton Lounge as a sort of late birthday present. The Baton is a famous drag show right in the heart of downtown . . . and within walking distance of our hotel. So there I was strolling down the streets of Chicago in my tights and heels – probably the farthest I’ve ever walked in heels before actually, but I was pretty proud that I made it with no problems :) I don’t go out crossdressing in public very often. In spite of the website, I’m still pretty nervous of people staring at me. Plus I don’t like to do it unless I’m traveling – have to keep up appearances with the neighbors (and co-workers, etc) if I’m out in public in my hometown! I do make an occasional exception for a little local drag show, but it’s not the sort of place I can hang out at every weekend.

    The Baton in Chicago is a bit past its heyday, and the drinks are super overpriced . . . but overall it was still a good time. The place was packed for the show, and it was clearly a serious production for the performers – this wasn’t your typical hole-in-the-wall bar type of drag show. One of the girls was drop dead gorgeous too. Service is a bit crappy, but the staff seemed to appreciate the fact that I had dressed up – it was definitely a comfortable place to be dressed. The one downside is that they don’t allow photography – I had all these plans of taking a bunch of pics of me crossdressing at the show, but unfortunately I had to keep the camera hidden :(

    Crossdressing in Downtown Chicago
    The rest of downtown wasn’t quite as comfortable – I got a couple interesting looks on the street. But it still didn’t keep us from stopping for a few photos on the bridge over the Chicago River. Overall I was impressed though – I guess you see all types in a big city like Chicago – most people didn’t bat an eyelash at passing a crossdresser on the street. I wasn’t exactly at my most passable that night. I’ve been trying to grow my natural hair out so I don’t always need a wig, but the pigtails perhaps weren’t the best choice for fitting in. Oops :P Ah well, the only particularly nerve-wracking part was walking back in through the hotel lobby and waiting on the elevator with a large crowd of people. Would I do it again though? Absolutely!

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